Hydroquinone → HCID 71613318, compound

HRID 1053563Notes

Reaction equation

HRID 1053563 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH:11]([CH3:13])[CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[C:20]1([CH:27]=[CH:26][C:24]([OH:25])=[CH:23][CH:22]=1)[OH:21]>CN(C=O)C>[CH:11]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][O:21][C:20]1[CH:27]=[CH:26][C:24]([OH:25])=[CH:23][CH:22]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 13955455N-(2-Chloroethyl)-N-(propan-2-yl)aniline

Product 1

HCID 71613318HCID 71613318, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 4c (400 mg, 2 mmol), K2CO3 (558 mg, 4 mmol), and KI (720 mg, 4 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (440 mg, 4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with CH2Cl2 and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide compound 4 (210 mg, 0.77 mmol, 38.3% yield) as a brown oil. HRMS (ESI, positive) m/z calcd. for C17H22N1O2 [M+H]+: 272.16451, found: 272.16455. 1H NMR (400 MHz, CDCl3) δ 7.16-7.05 (m, 2H), 6.75-6.56 (m, 7H), 4.08-3.83 (m, 4H), 3.50-3.42 (t, J=7.1 Hz, 1H), 1.19-1.06 (m, 6H).

Workup

  1. additionwas added to the mixture under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mL water
  6. extractionThe mixture was then extracted with CH2Cl2
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine and was dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5121d14fb004e87804c8dff5ae7118f
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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